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Tailscale

Manager, Commercial Expansion

Tailscale · Hybrid (Toronto, Ontario)

Posted about 2 months ago · $50,000-$100,000

or apply directly on Tailscale's site. We never take the application ourselves.

Is this posting real?

This role has been open
71 days
Tailscale's roles stay open a median of 76 days
Reposted
No
Salary listed
Yes
2% of Tailscale's roles list one
Ghost-job risk at Tailscale
high
60 stale, 2 reposted of 60 open
Hiring momentum
113 roles opened in the last 90 days
↑ up vs. the prior 90 days
Last confirmed on the employer's board
2026-10-22

Measured from postings appearing on and disappearing from Tailscale's own greenhouse board since 2026-08-03. Full hiring picture for Tailscale.

About this role

The Manager, Commercial Expansion at Tailscale will lead a sales team focused on existing customers in the Commercial segment. Responsibilities include prospecting, coaching team members, refining sales practices, and collaborating with other departments to generate and accelerate sales opportunities. This role is pivotal in establishing a new sales hub in Toronto and requires a hands-on approach to building a successful sales strategy.

Our read on this posting3.4out of 5
benefits
3/5
freshness
1/5
career value
4/5
role clarity
4/5
pay transparency
5/5

Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of Tailscale as an employer.

What you need

  • 1+ years of sales management experience in a B2B SaaS/Software company
  • Aptitude for delivering world-class customer experiences
  • Excellent written and verbal communication skills
  • Ability to manage many activities and tasks simultaneously
  • Ability to travel to industry events once a quarter

What you get

  • Comprehensive group benefits with no waiting period
  • Employer-funded retirement contributions
  • Support for personal and professional development
  • Paid time off and a healthy work-life integration
  • A build-your-own home office setup
  • Paid parental leave program

Worth weighing

  • Hybrid work model requires 3 days/week in-office presence
  • First sales leader role in a new hub may involve building processes from scratch
  • No specific mention of team size or structure for the sales team

Summarised from Tailscale's posting. Read the full original.

Listed by Tailscale on their greenhouse job board, last confirmed open on 2026-10-22. PitchMeAI is not the employer.

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